Synthesis of 2,6-Diamino-2,6-dideoxy-L-idose

✍ Scribed by Dr. W. Meyer zu Reckendorf

• Publisher: John Wiley and Sons
• Year: 1963
• Tongue: English
• Weight: 119 KB
• Volume: 2
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196303981

✦ Synopsis

carbene and lithium chloride. Finally, the carbene adds onto the olefinic double bond .

H, ,0-R

F,

(1) R = a l k y l

:c-c<

The formation of the cyclopropane derivative takes place in a stereospecific manner as ii cis-addition. I -Vinyl-2-rr-hexoxycyclopropune: A solution iwether of 0.14 mole of methyl-lithium (prepared from methyl iodide -~ a 1.2 N solution) is added dropwise over 2 hours at -5 "C to a stirred solution of 18.5 g (0. I mole) of dichloromethyl n-hexyl ether in 100 ml of butadiene. After hydrolysis with 100 ml of water, the ether layer is separated off, thoroughly washed with water, and dried over calcium chloride. Distillation yields 12.7 g of I-vinyl-2-n-hexoxycyclopropane, b. p. 122 OC/65 mm (isomer ratio 1.3 : 1).